Homoveratrylamine → N-(3,4-Dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide

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Reaction Steps

21.7 g of 2-(3,4-dimethoxyphenyl)ethylamine are dissolved in 150 cc of anhydrous chloroform and then the solution is added to 15.2 g of anhydrous triethylamine. The solution is cooled at a temperature between 5° and 10° C. and then, under stirring, there is added the 3,4-dimethoxyphenylacetyl chloride prepared in part (a), 26 g, dissolved in 80 cc of anhydrous chloroform. The temperature is allowed to rise to room temperature. It is then warmed under reflux for eight hours. After cooling the mixture, by addition of an additional portion of chloroform, 200 cc, the organic phase is washed with water and then with 5% hydrochloric acid and an additional amount of water, then 5% sodium hydroxide and finally water. The organic phase is dried over anhydrous sodium sulfate and after filtering, the solvent is evaporated under reduced pressure. The solid thus obtained is recrystallized from absolute ethanol. The pure amide, 36 g, is obtained in a yield of 84%, m.p. 128° C. The substance gives a single spot on chromatography using ethanol as eluent.

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